The Best Laid Plans
by Laurel West
Summary: Schemes, hijinks, plots, and gimmicks. Jackson’s bag of tricks is full of them. Especially when it comes to getting the girls. JacksonOC.
1. Chapter 1

My first ever _Hannah Montana _story!

Please read and review. Any critiques/corrections would be greatly appreciated.

Enjoy!

The Best-Laid Plans

Schemes, hijinks, plots, and gimmicks; Jackson's bag of tricks is full of them. Especially when it comes to getting the girls. He'll try anything - _anything_ - to impress them, to woo them, to win them. From offering to tutor a girl in Spanish (even though he himself was hardly passing), to pretending to be a racecar driver (leather jumpsuit - _not_ comfortable), to just plain begging, there's little Jackson hasn't done to get a date.

But _a_ date (just one, sometimes even less than that) is all Jackson ever gets, though not for lack of trying. He just somehow always messes it up. A scheme backfires, lies get jumbled, and before long he finds himself tripping over words trying to sort things out. Every date begins as a first and ends as a last.

"Maybe you should just try being yourself. You know, find a girl who'll like you just for being you, not some guy you pretend to be." Miley remarked one day.

It was a rare insight for Jackson. So much so, it actually gave him pause. But, how did that work? Being yourself. Making himself out to be something he's not was all he knew.

Why did he do that? To be impressive. But who was he trying to impress? Girls. Well, not just any girls. The seemingly unattainable ones. The more gorgeous, glamorous, and popular the girls, the more appealing they were to Jackson. Whenever such a girl came around, he turned into a circus animal - willing to do anything to get their attention.

But what about regular girls? Not the weird or scary ones, but not the fashionistas either. Those girls that Jackson never even really gave a second thought. Like… Breanne.

She sits on the side of the classroom, gets good grades, plays volleyball, and has never worn neon-colored anything. Her dark blonde hair's styled the same way every day, just straight and down past her shoulders, her bangs swept to the side and tucked behind her ear. She doesn't wear nail-polish, or jewelry, except for small earrings. She's not at all what you'd call popular, but she's no social pariah either. She's kinda just… there. Which is why - despite her pretty face and friendly disposition - she'd never before been the object of Jackson's pursuits.

Jackson tapped the eraser of his pencil on the corner of his desk. He barely heard his teacher as she lectured at the front of the classroom. Without much thought, he glanced to his left, and let his eyes rest on Breanne. She was wearing navy blue and grey, blue jeans, and flip flops. Her hair fell across her shoulder and onto her desk when she leaned forward to write in her notebook.

An idea occurred to Jackson as he gazed at Breanne, and that was - if he asked her out, she'd probably say yes. Not because he'd pulled some big stunt to show off, or because he was such a stud no girl could refuse, but simply because… she was nice. Breanne was a nice, regular girl. And a cute girl, in her own modest way.

By the time the bell rang Jackson had made up his mind. He was going to try this "being himself" thing. But he was gonna try it with someone safe, someone over whom he wouldn't be broken up if he ruined things.

"Hey, Breanne."

Breanne looked up from putting her notebook back into her backpack. She blinked at Jackson, then smiled politely.

"Hi, Jackson."

"How 'bout class today, huh?" He offered. Breanne kept her polite smile.

"Not the most entertaining lecture I've heard." She agreed.

"Yeah, you got that right. So… how are you doing in this class?"

At this point, Jackson felt to be grasping at straws. He hadn't thought much about what he'd say beyond "hey, Breanne", and was now seeing that maybe completely abandoning planning wasn't the best idea.

Breanne didn't seem to notice though, she just smiled a little more, "Pretty well. Why, you need a tutor?"

A little light bulb went on in Jackson's brain. A tutor! Yeah! No, wait… He didn't really need a tutor, he was doing okay in English. If he asked Breanne to tutor him, that would a gimmick, and he was trying to work without those.

He shook his head, "No, actually, I'm okay. I was just making small talk."

Breanne lifted an eyebrow, "Small talk? Like, you want to talk about the weather next?"

"No," Jackson almost laughed, "No, more like beating around the bush. I actually wanted to ask you something."

Breanne's other eyebrow raised, but she quickly changed her expression to be neutral.

"Okay, ask away."

"Well, I wanted to know if you'd go out with me this Friday."

Her eyes widened just the tiniest bit, and Jackson actually felt a slight clench in his stomach. Was he wrong? Would she not say yes? Well, it wouldn't matter too much if she did say no, it's not like he was really interested in her. He was just experimenting.

After a moment's hesitation, she nodded.

"Okay." She said. "Sure."

Jackson was surprised to feel a little relieved.

"Great." He grinned. "Well, I was thinking we could - "

"Just one thing," Breanne interrupted, "I have to ask. Why me?"

It was Jackson's turn to baulk. He hadn't expected that one.

"Well," He started, about to tell her 'I like you, of course', but that wasn't the most truthful statement. He liked her, sure, but not like all the other girls he'd asked out. But then, he couldn't tell her that, either. He finally settled with, "I'm curious."

Her nod seemed to indicate she'd take that answer for now. Again a little relieved, Jackson moved on.

"So, I was thinking I'd pick you up around 7?"

---

_That's all for now; please leave a comment if you want more!_


	2. Chapter 2

Thank you for the kind reviews! Here's more; I hope you enjoy!

---

Jackson tugged at the hem of his shirt as he stood outside Breanne's house. He felt strangely nervous. Usually when he picked up a date he was brimming with confidence, giddy to have managed to get the girl, if only for the night. This time was different, though.

He hadn't spent 30 minutes on his wardrobe and an hour on his hair like he usually did, just threw on the first clean outfit he found in his closet and did a quick shoosh of his bangs. He brushed his teeth, but skipped the mouthwash and floss, didn't practice his lines in the mirror, or kissing with his pillow. He didn't even pump up his radio on the drive over. He felt severely under-prepared, and wondered if he'd tried too hard not to try too hard.

At that moment the front door opened, and Jackson's attention was brought back to the present. Breanne stood in the doorway, backlighting from the hall giving her a glowing appearance.

"Hey." She smiled.

"Hey." Jackson blinked, and she stepped onto the stoop, pulling the door shut and allowing him to get a better look at her.

She looked the same as she always did, wearing a casual top, jeans, and sandals. And lip-gloss, Jackson noticed. That was new.

His instincts told him now was the time for a line. Something like, "Did it hurt when you fell from Heaven?"

"You look nice." Is what he said instead. And he meant it. She did look nice. As always. Nice old Breanne.

"Thank you." She smiled again. "So do you."

_You know it, baby._

"Thanks. Shall we get going?" Jackson shook his head as he led her down the walkway. This was already proving to be harder than he thought.

---

Jackson picked at his cotton candy as he sat on a bench and watched Breanne throw another baseball and knock down another pyramid of bottles. He glanced at his watch. He really wasn't having any fun.

It wasn't Breanne, though. She was fine. Pleasant and amicable, she was even showing a cute sense of humor. But Jackson wasn't enjoying a minute of her company because he'd been spending the whole night fighting with himself. Every time he felt the urge to crack a joke, pull a stunt, make a move, or show off, he didn't. He wouldn't. He had to be himself.

At the game with water guns, Jackson wanted to win Breanne a stuffed animal, but decided to let her beat him. On top of the ferris wheel he wanted to throw his arms up and yell, "I'm the king of the world!", but he just sat still. He'd wanted to splash around in the "Pick-a-Duck, Win-a-Buck" pond, ride the kiddy roller coaster, take pig-nosed pictures in the photo booth, throw popcorn at passers-by, and put his arm around Breanne's waist. But he didn't.

As he chucked the last of his cotton candy into the waste bin next to him, Jackson decided he himself was a pretty boring guy.

"Look at this giraffe I won!" Breanne grinned, returned from the booth and holding up a small stuffed animal. "I either have a good arm and good aim, or I'm just one lucky gal."

_I'm the lucky one, here with a girl like you._

"Yeah, lucky you." Jackson agreed, with little enthusiasm. "Hey, it's getting kinda late. I should probably get you back home. Wouldn't want your parents to be upset."

Breanne's grin faded the slightest bit.

"Oh, yeah. My dad does worry."

The ride back to Breanne's house was quiet. She tried to make some small talk, but gave up when Jackson responded only in monosyllables. She just looked at the stuffed giraffe in her lap.

"I think I'll name him Stewart." She said after a while. Jackson glanced at her. "You know, to remember where I was and who I was with when I won him."

Jackson almost smiled.

"I had a good time, tonight, Jackson." Breanne said genuinely when they made it to her doorstep.

"Yeah, me too." Jackson answered automatically, not meeting her gaze.

"So, did you satisfy your curiosity or do we need to maybe do this again sometime?"

Jackson looked up at Breanne. She was smiling, and he just couldn't understand why. He'd been probably the worst date ever tonight. She should be angry with him. She should kick him in the shin, storm inside, and never speak to him again. At least, she shouldn't be asking for another date. That was just… not how it worked. It was not what he was used to.

"Well?" Breanne smiled like she found his blank stare amusing, and Jackson noticed her eyes were green.

He then got the urge to kiss her. Sweet nibblets, he wanted to kiss her! And he had no idea why.

"Yeah," He finally said. "Let's do this again sometime."

As he walked away, he could feel her grinning as she watched him, and he wondered if maybe he hadn't gone about this all wrong.

---

_Please review if you want more!_


	3. Chapter 3

_Thank you for the kind reviews! Keep 'em coming and I'll keep coming with the story!_

---

The first rays of the rising sun were spilling in through the blinds of Jackson's window. He was in his bed, but still fully clothed, his blankets and pillow strewn about, his feet at the head of the bed and his head at the foot.

He wasn't sure if he'd slept. He didn't think he did, but if he hadn't, where had the hours gone? He couldn't really have stayed up all night thinking about…

Well, what didn't he think about? He thought about the carnival. Breanne. Miley said just be himself. But did that mean not to act the way he always did? He could have beaten Breanne at that stupid water gun game. Was he trying so hard to be himself he was being someone he's not? He'd wanted to kiss her. He didn't even like her like that.

She'd been standing in front of him on the doorstep, smiling. Her eyes were green and her skin smooth and her hair danced across her face in the light breeze. Her lip gloss had worn off through the night, but her lips were still blushing.

Okay, so she's pretty. She has a nice smile and she shows it often. And she didn't kick him in the shin. Why was she so nice?

Jackson had never dated a nice girl before. Vapid, shallow, brainless, trampy, catty, and selfish, sure. But nice? That would be the last word he'd use to describe any of the girls he'd been with. And it was the one word he kept coming back to with Breanne.

---

"Hey, Breanne." Breanne looked around her locker door to see Jackson. She smiled warmly.

"Hey, Jackson. How was your weekend?" She asked, getting a few books out of her locker.

"Long. And… quiet. And long." Was all he could muster. Breanne paused to look at him.

"Something up?" She asked, her smile fading.

"Listen, Breanne, I've been thinking," Jackson started, silently pleading with himself not to botch this.

"Oh, that's not good."

"No, I mean, it's not - " He was going to explain that what he had to say wasn't anything bad, but then he realized she was grinning at him.

She was teasing him. In other words… flirting.

"I want to apologize." He blurted. Now she looked confused.

"For what?"

"For Friday. For the date. For everything." He bit his lip. He couldn't believe what he was saying. Neither could Breanne.

"What are you talking about?" A hint of a smile was tugging at her lips. "I had a good time. You were a lot quieter than I expected, but that's okay."

"No," Jackson shook his head. She wasn't getting it. "I mean, I'm sorry I asked you out."

Now she looked really confused.

"I, no, I don't mean it like that, it's just - I haven't been myself lately. I… I wasn't myself with you."

Breanne blinked at him, waited for him to continue.

"See, truth is… I don't like you."

As soon as the words came out of his mouth and a look of quiet hurt crossed Breanne's face, Jackson kicked himself.

"Wait, that came out wrong. No, I like you, I do, just… when I asked you out it wasn't 'cause I wanted to go out with you."

"Why did you then?" Breanne asked quietly. It was a good question. One Jackson had been wondering all weekend how to answer.

"Because I knew you'd say yes." He sighed. At that moment the bell rang, and students began filing out of the hallway. "Look, Breanne, I wasn't honest with you and I'm sorry. I just want to know if we could start over. I'd like to take you out again, and be myself this time."

It was true. He had no idea why, but he wanted a do-over. He wanted to go on another date with Breanne, but this time he was going to throw popcorn at passers-by. And see if she wouldn't start being annoyed by him like she was supposed to.

"I said yes just to be nice." Breanne finally replied.

"I know."

She gave Jackson an appraising look, then sighed, "If you came by my house tonight around 6, I might be home."

He watched as she disappeared down the hall. He didn't understand any of it. Again, she should have kicked him in the shin. So why didn't she? And why did he feel like if she just would he could forget about her?


End file.
